The chalcogen–nitrogen bond (X–N, where X = S, Se) is a key chemical motif in many structures, including inorganic and organic materials, catalysts, protein mimics, and pharmaceuticals. Consequently, developing mild and general methods for constructing N–S and N–Se bonds is important in organic synthesis. Herein, we have developed a novel copper-catalyzed approach to form N–S/N–Se bonds by coupling amines with 1,2-diphenyl disulfide or diphenyl diselenide. The disclosed platforms demonstrate excellent substrate scope, delivering the desired products in good to excellent yields, and are readily amenable for scale-up. The configuration of the product was confirmed through single-crystal X-ray diffraction analysis. Hitherto, no prior reports have been found in the literature for forming N–Se bonds making this reaction an important breakthrough in synthetic organic chemistry.

中文翻译：

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苯胺的铜催化 N-H 键硫化反应


硫属-氮键（X–N，其中 X = S， Se）是许多结构中的关键化学基序，包括无机和有机材料、催化剂、蛋白质模拟物和药物。因此，开发构建 N-S 和 N-Se 键的温和和通用方法在有机合成中很重要。在此，我们开发了一种新的铜催化方法，通过将胺与 1,2-二苯基二硫化物或二苯基二硒化物偶联来形成 N-S/N-Se 键。所披露的平台表现出优异的底物范围，以良好到优异的产量提供所需的产品，并且很容易进行放大。通过单晶 X 射线衍射分析确认了产品的构型。迄今为止，文献中没有发现形成 N-Se 键的先前报道，使该反应成为合成有机化学的重要突破。